Destination Guide: Boston

I've grown up in the 'burbs here in Massachusetts and taken Boston for granted. It's a walkable, toddler-friendly city with tons of stuff to do.

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I grew up 26.2 miles outside of Boston in Hopkinton, the start of the Boston Marathon. Growing up we would go into the city for Special Occasions and mostly when out-of-towners came to visit us. We’d do places like the Museum of Science (one of my favorite museums EVER) or the Symphony and then skedaddle. It wasn’t until I got to my first Big Girl college internship downtown that I started to get to know the city—after years of commuting in different ways, now it feels “mine.”

The iconic Citgo sign, taken from one of my Boston Marathon training runs. (No I did not qualify lololol)

This destination guide is the culmination of thousands of hours of living both as a suburban tourist and a daily commuter. I’ve added our exact itinerary for our annual staycation, my favorite restaurants, and notes on different neighborhoods.

You should skip Boston if…

• You’re on a budget. Boston is one of the most expensive cities in the U.S., alongside NYC and San Francisco. You’ll pay $100 for lunch for a family of four at a decent spot, easy.

• I would not visit Boston in the winter unless you’re there for family or as a stopover on the way to a ski vacation…the snow makes it difficult to push a stroller, and the cobblestones already make it hard!

• You’re a big foodie. I have included family-friendly spots to eat here, and there is good food if you know where to look…but the neighborhoods with the best sites for little ones don’t have a *ton* of options. The food scene has gotten much better in recent years, but it’s a long way to go before we’re anywhere close to NYC.

• You want to teach your kiddos about the Revolutionary War. If that’s the case, I’d wait a few years until they can really “get” the history stuff. Boston is one of the oldest cities in the U.S.—ever heard of the Boston Tea Party?—but that will go right over a toddler’s head, I think, so if you want to maximize the educational part, I’d wait until elementary school.

• You’re a Yankees fan. Getoutttaaheeeahhh! (Joking, joking.)

Why go: Boston is a historical destination with tons to see and do.

But! I love Boston so much. It’s a great, walkable city with vibrant green spaces, a rich history, and top-tier cultural attractions. Plenty of the stereotypes are true (there’s a Dunkin Donuts every 3 blocks, basically), and with babies and toddlers there’s a lot to see and do. You’ve got major tourist attractions worth checking off any list plus incredible art, music, and sports.

The Travel with Toddlers guide for more magic, less meltdowns

This guide contains:

• A neighborhood-by-neighborhood overview with where to stay, eat, and what to do

• My favorite playgrounds in the city and what delicious food is nearby

• The best restaurants for picky eaters

• Optional day trips to the ‘burbs to add on

• And more!!!

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Still with me? Welcome to a local’s guide for the best toddler trip to one of the U.S.’s oldest cities: